3944-09-0

Basic information

• Product Name: 1,1-diphenylsiletane
• Synonyms: 1,1-diphenylsiletane
• CAS NO: 3944-09-0
• Molecular Formula: C₁₅H₁₆Si
• Molecular Weight: 224.37304
• EINECS: -0
• Mol File: 3944-09-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,1-diphenylsiletane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-diphenylsiletane(3944-09-0)
• EPA Substance Registry System: 1,1-diphenylsiletane(3944-09-0)

Safety Data

• Hazardous Substances Data: 3944-09-0(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Solubility

Insoluble in water

Boiling point

302-304 degrees Celsius

Applications

a. Organic synthesis
b. Production of high-performance polymers
c. Precursor in the preparation of various silicon-containing compounds

Chemical reactions

a. Cross-coupling reactions

Versatility

Acts as a building block for the synthesis of complex organic molecules

Fields of application

a. Chemistry
b. Materials science
c. Pharmaceuticals

Upstream product

• 2351-33-9 1,1-dichlorosilacyclobutane 
• 108-86-1 bromobenzene 
• 2550-06-3 3-chloropropyltrichlorosilane 

Downstream Products

• 18767-30-1 1,1,2-triphenyl-1-silacyclopentane 
• 131472-82-7 2,2,6-triphenyl-1,2-oxasilinane 
• 131472-83-8 6-tert-butyl-2,2-diphenyl-1,2-oxasilinane 
• 135068-07-4 (E)-1,1,3-Triphenyl-3-sila-1,5-hexadiene 
• 135067-96-8 1,1,3-Triphenyl-1-sila-2-cyclohexene 
• 135068-06-3 Methyl (E)-3-(allyldiphenylsilyl)acrylate 
• 135067-95-7 Methyl 1,1-diphenyl-1-sila-2-cyclohexene-3-carboxylate 
• 135068-05-2 Methyl (E)-3-methoxycarbonyl-4,4-diphenyl-4-sila-2,6-heptadienoate 
• 135067-94-6 Dimethyl 1,1-diphenyl-1-sila-2-cyclohexene-2,3-dicarboxylate 
• 131473-05-7 2-iodo-1,1-diphenyl-1-silacyclopentane 
• 131473-07-9 2-chloro-1,1-diphenyl-1-silacyclopentane 
• 145474-99-3 1,1-diphenyl-2-trimethylsilyl-1-silacyclopentane 
• 135068-26-7 Allyldiphenyl(α-methylstyryl)silane 
• 135068-24-5 2-Benzylidene-1,1-diphenyl-1-silacyclohexane 

Relevant articles and documents

Palladium-Catalyzed Enantioselective Carbene Insertion into Carbon-Silicon Bonds of Silacyclobutanes

We report herein a highly efficient palladium-catalyzed carbene insertion into strained Si-C bonds with excellent enantioselectivity, which provides a rapid and distinct method to access silacyclopentanes with a three- or four-substituted stereocenter asymmetrically. Mechanistic studies using hybrid density functional theory suggest a catalytic cycle involving oxidative addition, carbene migratory insertion, and reductive elimination. In addition, roles of the chiral ligands in controlling the reaction enantioselectivity are also elucidated.

Rhodium-Catalyzed Reaction of Silacyclobutanes with Unactivated Alkynes to Afford Silacyclohexenes

A Rh-catalyzed reaction of silacyclobutanes (SCBs) with unactivated alkynes has been developed to form silacyclohexenes with high chemoselectivity. Good enantioselectivity at the stereogenic silicon center was achieved using a chiral phosphoramidite ligand. The resulting silacyclohexenes are useful scaffolds for synthesizing structurally attractive silacyclic compounds.

Oxidation of Carbon-Silicon Bonds: The Dramatic Advantage of Strained Siletanes

(Matrix presented) Herein we report on the use of siletanes as substrates for the oxidation of carbon-silicon bonds. These tetraalkylsilanes are easy to handle yet susceptible to rapid ring opening and oxidation upon exposure to aqueous fluoride and peroxide. This combination of stability and reactivity presents many practical benefits, including compatibility with silicon protecting groups and electron-rich aromatic rings.

Lithium Carbenoids Induced Ring Enlargement of Silicacyclobutane into 2-Halo-1-silacyclopentane and its Use in Organic Synthesis

An addition of lithium diisopropylamide to a solution of 1,1-dimethyl-1-silacyclobutane and dihalometane such as CH2I2, CH2Br2, or CH2Cl2 provided the corresponding 1,1-dimethyl-2-halo-1-silacyclopentane in good yield.The reactions of 1,1,2-trimethyl-1-si

Palladium Catalyzed Reaction of Silacyclobutanes with Acetylenes

Whereas the reaction of 1,1-dimethyl-1-silacyclobutane (1a) with dimethyl acetylenedicarboxylate in the presence of Pd catalyst provides dimethyl 1,1-dimethyl-1-sila-2-cyclohexene-2,3-dicarboxylate almost exclusively, the reaction of 1a with phenylacetyle

SILAETHENE I. DARSTELLUNG UND CHARAKTERISIERUNG VON MONOSILACYCLOBUTANEN

Monosilacyclobutanes of the type RR' are prepared by ring closure reactions of 3-halopropylhalosilanes and by substitution of SiCl containing silacyclobutane rings with organometallic reagents (RMgX, LiR, NaCp).Under optimal experimental conditions yields between 50 and 95percent can be obtained by both procedures.Characterization of the compounds is accomplished by analytical (C, H, N) and NMR, IR and mass spectroscopic investigations.